Yes, It's not just electronic communication either. A senior manager where my wife once worked wrote the code for the entry door keypad...on the keypad, because memorizing it (or writing it down on a piece of paper he would have to dig out of his pocket) was too much trouble. True story. (I'm sure you all have stories as bad or worse than this one.)

The CEO of a company I used to work for claimed the VPN was inconvenient, so he would basically sync our entire file server to his laptop every day - marketing, finance, development projects, the works. His laptops were also constantly being misplaced or stolen, so who know how many copies of everything we had are floating around out there. Every business trip was a major security breach in the making.

Have seen senior managers (CEO-level) saving their daily-to-do's emails in the TRASH!!

Back in the 90s, the company I worked for at the time, was a Novell+Groupwise shop, and we discovered that the company CEO was saving important email to the Groupwise trash. Found this out when we did a trash purge over a weekend and come Monday morning, CEO's executive assistant was on the phone to support saying that the "big-boss" lost a LOT of important email... I was the foot-soldier on call that day, so I had to run down to his office, and investigate. I had to fight hard to keep from laughing out loud when the assistant (big-wig was out of the office, but assistant had big-wigs password(s)) showed me just WHERE the emails had been stored, after a lot of prodding and question-asking.. Since I knew there had been a Groupwise trash purge over the weekend, I knew exactly where the mail had gone, but hoping against hope that the Novell salvage had not been cleared yet, I called the desk admin, and fortuantly he was JUST getting ready to clear salvage.. I managed to stop him, and we were able to recover the big-wigs email.. Being I was the new-guy, there was NOOOOO way I was gonna tell the CEO and his assistant "you DO NOT PUT EMAIL YOU WANT TO KEEP IN THE TRASH!!!".. I left that up to my big-boss, the CIO... Needless to say we had many chuckles at the next months team meeting...